You don't need to do that much cafe jobs to max the relationships with the master.So the only way to get to date him is to finish the game once first ? And then dating him is just an ending too ? Kinda a lot of grind for not much. I couldn't even edit his progress via save editor since it's well encrypted :/ I am at day 70, and it feels like i don't move with him since the dev put no detail of the evolution of the relation besides random events.
What you do need is the skill you get from the dancing crab at night.
And money, which if you are doing a virgin run is kind of hard, I recommend a slut run for the first playthrough and then reset with New Game+ after the ending.
You just skip time with that skill till 365 to get to the ending.
But if you do get the Master ending you can continue the game and date him and even get pregnant.